Motor fuel of high antiknock value



Patented Dec. 3, 1935 I 2,023,142 MOTOR FUEL or men an'mmocx VALUE Nlcolaas Max, Amsterdam, Netherlands, asslgnor to Shell Development Company, San Francisco, Calil'., a corporation of Delaware No Drawing. Application September 14, 1932,

Serial No. 633,079. In the Netherlands September 22, 1931 10 Claims.

The invention relates to a processfor the production of motor fuels of high anti-knock value.

It is known to improve the anti-knock value of motor fuels by the addition of a great many substances which are volatile at the working temperature of the engine, i. e. organic compounds of various metals and metalloids.

According to the invention motor fuels of high anti-knock value are produced by adding to the fuel, for examplegasoline and similar fuels for ignition motors, metal compounds of the condensation products of compounds which besides one carbonyl group contain one or more of oxygen-containing radicals in the molecule with amines. Thus, to the motor fuel may be added heavy metal salts of the condensation products of oxy-aldehydes, di-ketones, tri-ketones and the like with primary amines. The components of the condensation product may be of an aliphatic as well as of an aromatic nature.

The metal compounds which are primarily suitable are, generally speaking,'those heavy metal salts the metals of which can form with ammonia complex compounds such as copper-, nickel-, cobalt-, zinc-, chromiumand similar salts.

Of the known substances-hitherto used as antiknock media the metal salts of p di-ketones come nearest in composition to the substances according to the invention. A drawback of using these metal salts as anti-knock media lies in their low solubility in benzines which contain few aromatic hydrocarbons. For this reason it has been endeavoured to increase the solubility by the addition of aromatic hydrocarbons, alcohols and the like. The compounds used according to the invention are more soluble in benzine even if this benzine contains comparatively small amounts of aromatic hydrocarbons.

The following examples of compounds to be used may i. e. be mentioned: the copper-, nickeland cobalt compounds of salicylal-allylamine, salicylalmethylamine, 3 naphtholal-allylamine, protocatechual-ethylamine and the condensation product of allylamine andacetyl acetone, etc.

The following are a few methods of preparing these compounds:

(a) Production of salicylal-allylamine copper 5.7 g. allylamine is added to 12.2 g. salicylaldehyde whilst shaking. With a strong development hol, gives with an equivalent quantity "of copper acetate in a concentrated aqueous solution a precipitate of salicylal-allylamine copper which is at first oily but subsequently crystallizes. The compound itself forms good dark green needles which can be dissolved in practically all organic solvents; melting point 114-116 0., Cu-content according to analysis 15.0%, theoretically for CzoHzoNaOzCu 15.3%.

(6) Production of 0-3 naphtholal-methylamine copper According to the Gattermann method the hydrochloric acid imino-ether of the oxaldehyde is prepared from p-naphthol with hydrocyanic acid and HCl in an absolutely etheric solution, from which, by boiling with water, the Op n'aphthol aldehyde is obtained. Methylamine gas is introduced into a methylalcoholic solution of this aldehyde, resulting in the productionof the 0-5 naphtholal-methylamine. From this the copper compound is obtained with copper acetate in the manner described under (a).

It appears that at least a portion of condensationproducts, which result from reactions of primary alkyl amines with alkyl and/ or aryl ketoand/or aldo-compounds having one or more substituted oxygen atoms in their molecules besides at least one carbonyl group, may be represented by the formula:

in which R1 represents either an alkyl grouping wherein M represents a heavy metal and a: corresponds to the valence of the metal.

The following examples illustrate the process according to the invention:

Example I To a benzine with which was admixed 5% benzol and having a Ricardo variable compression engine H. U. C. of 5.40, 0.05% copper in the form of sailcylal-methylamine-copper was added, a H.- U. C. of 6.45 thus being obtained.

wherein R1 represents an alkyl grouping or hydrogen, R2 designates a hydrocarbon grouping directly linked to at least one hydroxyl or carbonyl group other than that contained in a carboxylic acid, and R3 is an aliphatic radical, said heavy metal being capable of forming a complex compound with ammonia.

3. A gasoline type motor fuel comprising a substantial proportion of a hydrocarbon fuel mixture containing a small quantity of a heavy metal compound of the compound having the structural formula:

wherein R1 represents an alkyl grouping or hydrogen, R: designates a hydrocarbon grouping linked to at least one keto group, and R: is an alkyl grouping, said heavy metal being capable of forming a complex compound with ammonia.

4. A gasoline type motor fuel comprising a substantial proportion of a hydrocarbon fuel mixture containing a small quantity of a heavy metal compound of the compound having the structural formula:

O=N-Ru Example II wherein R1 represents H, R: designates "1b a benzine with which was admixed 10% OH bemol and having a H. U. C. of 5.46, 0.06% cobalt in the form of salicylal-allylamine-cobalt was added, a H. U. C. of 6.48 thus being obtained. 5

Example III To a benzine having a H. U. C. of 5.47, 0.02% and R3 is an alkyl or aryl grouping, said heavy copper was added in the form of salicylal-allylameta] being capable f f rming a complex mine-copper, a H. U. C. of 5.72 thus being obpound with ammonia 10 5; A gasoline type motor fuel comprising a sub- Besldes the metal mp0unds other stantial proportion of a hydrocarbon fuel mixture stances, such as compounds preventing deposicontaining a Small quantity of a heavy metal tion of metal on the valves of the engine and/or compound of the compound having the structural r other anti-knock media may be simultaneously f r ula; 10 added to the motor fuel. R

What I claim is:

1. A gasoline type motor fuel comprising a sub- =stantial proportion of a hydrocarbon fuel mix- R: 20

ture containing a small quantity of a heavy metal a compound of the compound having the structural wherein R1 .Iepresent" (.lesignatas formula: on

C-N-R: 25

and R3 is an alkyl grouping, said heavy metal being capable of forming a complex compound with ammonia.

6. A gasoline type motor fuel comprising a substantial proportion of a hydrocarbon fuel mixture containing a small quantity of a heavy metal compound of the compound having the structural formula:

C=NR| Ra wherein R1 represents CH1 and R: designates o can't-cm 5 and R: is an alkyl grouping, said heavy metal being capable of forming a complex compound with ammonia.

7. A gasoline type motor fuel comprising a substantial proportion of a hydrocarbon fuel mixturecontaining a small quantity of a heavy metal compound of salicylal-allylamine, said heavy metal being capable of forming a complex compound with ammonia.

8. A gasoline type motor fuel comprising a substantial proportion of a hydrocarbon fuel mixture containing a small quantity of a copper compound of salicylal-allylamine.

9. A'gasoline type motor fuel comprising a substantial proportion of a hydrocarbon fuel mixture containing a small quantity of a heavy metal compound of protocatechual-ethylamine, said heavy metal being capable of forming a complex compound with ammonia.

10. A gasoline type motor fuel comprising a as substantial proportion of a hydrocarbon fuel mixture containing a small quantity of a heavy metal compound of acetylacetylacetone allylamine, said heavy metal being capable of forming a complex compound with ammonia.

NICOLAAS MAX. 

